Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6‐(Diisopropylamino)‐1‐azafulvene Derivatives. Novel synthesis of 5‐mono‐ and 4,5‐disubstituted 1 H ‐pyrrole‐2‐carbaldehydes | Zendy

Bray Brian L. | Zendy; Hess Petr | Zendy; Muchowski Joseph M. | Zendy; Scheller Markus E. | Zendy

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Lithiated Azafulvenes by Halogen/Metal Interchange of Brominated 6‐(Diisopropylamino)‐1‐azafulvene Derivatives. Novel synthesis of 5‐mono‐ and 4,5‐disubstituted 1 H ‐pyrrole‐2‐carbaldehydes

Author(s) -

Bray Brian L.,

Hess Petr,

Muchowski Joseph M.,

Scheller Markus E.

Publication year - 1988

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19880710823

Subject(s) - chemistry , halogen , pyrrole , reagent , hydrolysis , metal , organic chemistry , bromine , combinatorial chemistry , medicinal chemistry , alkyl

The first known lithiated 1‐azafulvene derivatives were generated by low‐temperature halogen/metal interchange, with t ‐BuLi, from the corresponding brominated 6‐diisopropylamino compounds 3b and 12 . These Li species reacted with sundry eletrophilic reagents to give products which, on basic hydrolysis, were converted into 5‐mono‐ or 4,5‐disubstituted pyrrole‐2‐carbaldehydes 10 and 16 , respectively.

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